170956-17-9Relevant academic research and scientific papers
Short and efficient synthesis of optically active N-tosyl aziridines from 2-amino alcohols
Bieber, Lothar W.,De Araujo, Maria C. F.
, p. 902 - 906 (2007/10/03)
Two alternative and complementary one-pot procedures for the direct transformation of 2-amino alcohols to N-tosyl aziridines are presented. The unsubstituted parent compound and its less hindered homologues can be obtained in high yields by tosylation and
Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer
Oka, Takahiro,Yasusa, Takuya,Ando, Takashi,Watanabe, Mayumi,Yoneda, Fumio,Ishida, Toshimasa,Knoll, Joseph
, p. 1213 - 1219 (2007/10/03)
Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.
Efficient asymmetric synthesis of pumiliotoxin C via intramolecular [4 + 2] cycloaddition
Oppolzer, Wolfgang,Flaskamp, Elmar,Bieber, Lothar W.
, p. 141 - 145 (2007/10/03)
An efficient asymmetric synthesis in nine steps of natural (-)-pumiliotoxin C (1), a decahydroquinoline alkaloid found in the skin of Central American frog species, is presented. The enantiomerically pure starting material (S)-norvalinol (3) obtained from
Synthesis of macrocyclic insect-derived alkaloids
Farmer, Jay J.,Schroeder, Frank C.,Meinwald, Jerrold
, p. 2594 - 2606 (2007/10/03)
Macrocyclic lactonic alkaloids found in the pupal secretions of two species of a coccinellid beetle (genus Epilachna) were prepared in enantiomerically pure form via an efficient synthetic route using enantiomerically pure α-amino acids as chiral-pool starting materials. Macrocycles with rings containing up to 98 atoms were synthesized in good yield using Mukaiyama's macrolactonization conditions.
Absolute configuration of insect-produced epilachnene
Farmer, Jay J.,Attygalle, Athula B.,Smedley, Scott R.,Eisner, Thomas,Meinwald, Jerrold
, p. 2787 - 2790 (2007/10/03)
Samples of (X) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en olide] were synthesized from (R) and (S)-norvaline. The diastereomeric α-methoxy-α-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) α-methoxy-α-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene.
Addition of dimethyloxosulfonium methylide to enantiomerically pure sulfinimines: Asymmetric synthesis of 2-substituted aziridines
Davis,Zhou,Liang,Reddy
, p. 1511 - 1514 (2007/10/02)
Diastereoselective addition of dimethyloxosulfonium methylide to chiral nonracemic pure sulfinimines 1 affords N-sulfinyl aziridines 3 in 58-70% de which are readily separated. The N-sulfinyl auxillary in 3 was removed, without ring-opening, by treatment
